Process for the preparation of substituted divinylpyridines and

Details Process for the preparation of substituted divinylpyridines and Process for the preparation of substituted divinylpyridines and

1983-01-17

1984-10-16

Bond, Robert T.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546350, 546 22, 546250, 546253, 546346, 546352, C07D21330, C07D21316, C07D21326, C07D21357

Patent

active

044776730

ABSTRACT:
The invention relates to compounds of the formula I ##STR1## wherein R' is bound in the 4- or 5-position, R and R' are --CH.sub.2 OH, --CH.sub.2 CH.sub.2 OH, --CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5, --CH.sub.2 --X, --CH.sub.2 P.sup..sym. (Y).sub.3 X.sup..crclbar., --CH.sub.2 P(O)(C.sub.1-3 alkoxy).sub.2 or --CH.dbd.CH.sub.2, R" is C.sub.1-10 alkyl, X is a halogen atom, X.sup..crclbar. is the anion corresponding to X and Y is phenyl or phenyl which is substituted by a C.sub.1 -C.sub.5 alkyl group. These compounds can be obtained by a novel simple process in good to very good yield by co-cyclotrimerizing nitriles R"--CN with alkynes HC.dbd.C--Z (Z is --CH.sub.2 OH, --CH.sub.2 CH.sub.2 OH or --CH.sub.2 CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5), in the presence of a cobalt(I) catalyst, dehydrating the resultant pyridines either to compounds of the formula I, in which R and R" are --CH.dbd.CH.sub.2, or converting them into the corresponding bishalomethylpyridines, reacting these latter with triphenylphosphines or trialkylphosphites and subjecting the pyridinephosphonium salts or pyridinephosphonic acid tetraalkyl esters so obtained to a Wittig or Wittig-Horner reaction. Compounds of the formula (I), in which R and R" are --CH.dbd.CH.sub.2, can also be obtained by direct reaction of nitriles R"--CN with vinyl acetylene in the presence of cobalt(I) catalysts, and are used e.g. as crosslinking agents or for the production of polymers.

REFERENCES:
patent: 3467663 (1969-09-01), Ineno et al.
patent: 4266061 (1981-05-01), Bonnemann et al.
Chemical Abstracts vol. 55, col. 18721i, (1961) Abstracting Bodalski et al. "Bull. Acad. Polon. Sci., Ser. Sci. Chim." vol. 8, pp. 217-218 (1960).

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